A succinct synthesis of the vaulted biaryl ligand vanol via a dienone-phenol rearrangement.
نویسندگان
چکیده
Vanol is a member of the vaulted biaryl family of ligands and it has been proven to be very effective in a number of asymmetric catalytic reactions. The previous synthesis of vanol, while effective, is limited by the cost of reagents involved. The present work evaluates three different approaches to the synthesis of 3-phenyl-1-naphthol, a key intermediate in the synthesis of vanol. The first approach has its key step as the Michael addition of a benzyl Grignard to methyl cinnamate. In the second approach the key step is the first step, a Reformatsky reaction of ethyl bromoacetate and deoxybenzoin. The final and most-efficient approach involves a dienone-phenol rearrangement of a 4-aryl-1-tetralenone generated in-situ from the reaction of 4-chloro-1-naphthol with AlCl(3) and benzene, and preliminary results are reported on the extension of this method to substituted vanol derivatives.
منابع مشابه
Scalable Syntheses of the Vaulted Biaryl Ligands VAPOL and VANOL via the Cycloaddition/Electrocyclization Cascade
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ورودعنوان ژورنال:
- Chemistry, an Asian journal
دوره 6 8 شماره
صفحات -
تاریخ انتشار 2011